


"Truth or Dare, Winchester?"

by BerylSpring



Category: Supernatural
Genre: Dom Dean, Dubious Consent, F/M, Hair-pulling, Light Bondage, One Shot, Oral Sex, Porn With Plot, Reader-Insert, Rough Sex, Situational Humiliation, Spanking, Truth or Dare
Language: English
Status: Completed
Published: 2016-03-17
Updated: 2016-03-17
Packaged: 2018-05-27 04:50:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,698
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6270259
Author URL: https://archiveofourown.org/users/BerylSpring/pseuds/BerylSpring
Summary: <blockquote class="userstuff">
              <p>You and some hunting buddies are staking out a werewolf pack, when the Winchesters show up.  With a pack this large, you can use every man you can get.  The problem is that you had a run in with the Winchesters before, and it didn’t leave the greatest impression.  You manage to set aside your differences until the hunt is over, but when you give the eldest Winchester a little pay back during a celebratory round of drinking amongst your allies, you may find it leads you to a much different, and more pleasurable, relationship with the handsome hunter.</p>
            </blockquote>





	"Truth or Dare, Winchester?"

**Author's Note:**

> Hi guys! This is my first reader-insert fic, so I hope you like it! It came out a little differently than I first imagined it in my head, but I think it holds up. Just a side note to anyone waiting on updates on my ongoing fics: I have been extremely busy these past few months with my internship putting in 15 hour days, so unfortunately my writing had to stay on the back burner. This is one quick fic that I could finally squeeze in. I am working (slowly) on my series and chapter fics as well as a sequel to a one-shot, but I probably won't get anything done until Easter break. Sorry for the delay, but I hope this one tides you over! Thanks guys!

You were halfway through interrogating a witness to the brutal slaying of a local bank manager when you noticed the black Impala roll up to the scene. As you listened to the witness’s statement, jotting notes down in a small, leather-bound notebook, you watched as the Winchester brothers flashed their fake FBI badges at the local sheriff. You were wearing your fake state trooper uniform, thinking you would only have to outrank the county sheriff, but now that the “feds” were there you were going to have to get your information and move out quickly. As you tried to finish up your questions, you saw the brothers heading towards you, a smug smirk of recognition plastered across the older Winchester’s face.

“Excuse me,” Dean said as he flashed his badge at your witness, “I’m agent DeYoung, this is Agent Shaw. We would like to ask you a few questions.”

It took all your strength not to blow you cover by punching that arrogant smile off his face. “I just have one more question for her, Agent, and then she’s all yours,” you said as respectfully as you could possibly muster.

“Oh I don’t think so, ma’am. This is officially a federal investigation now, but thanks for all your hard work.”

You narrowed your eyes at him slightly, and he met your gaze, obstinately challenging your competence. With a reluctant nod in his direction, you took your leave of the witness and headed towards the beige pickup that your buddy was waiting in down the street. When you climbed up into the driver’s seat, you slammed the door, hard.

“The FBI showed up, huh?” Josh, your companion, remarked.

You had met Josh a year ago on a hunt in San Francisco where you joined forces to eliminate a Rugaru. He was one of the most capable hunters you had ever worked with, and you teamed up from time to time on difficult cases. This case, what you believed was a werewolf pack the size of a football team, was a particularly nasty one, so Josh called in a few of his other buddies to help. There were five of you working the case.

With a sigh of frustration, you announced, “They aren’t FBI. They’re hunters!”

“Great!” Josh exclaimed, “We could use all hands on deck here!”

“NO!” you snapped, before taking a deep breath and regaining your composure, “We are not working with the Winchesters.”

“The Winchesters? As in Sam and Dean Winchester? Are you kidding me?” He asked excitedly, which got on your nerves, “Man, they’re like legendary!”

“We have enough people to handle this, we don’t need them. You know what they say about too many cooks in the kitchen?”

“Seriously, (Y/N), we’ve got a pack of werewolves on our hands! Don’t you think we have a better chance the more of us there are?” He questioned.

He wasn’t wrong. You certainly could use more hunters. It would be more efficient and less dangerous that way, but you were in charge here! You put this group together for this case, and you would be damned if you were going to let Dean Winchester undermine your authority! This wasn’t the first time you had encountered the Winchesters.

You had run into them on one of your first cases, and Dean had made it perfectly clear that you weren’t what he called “hunter material”. He had done everything he could to get in your way, making snide comments about your experience, or lack thereof, and he was reckless enough to land you in the hospital with a broken arm. The whole experience left a bad taste in your mouth, and you swore you would never work with the two of them again. Although, you had to admit, Sam wasn’t so bad. But if you worked with Sam, his brother inevitably came with him, so it wasn’t going to happen.

A knock on the window startled you out of your memory. You shot a look of annoyance back at the culprit and rolled the window down.

“Well, look who it is?” Dean said, eyeing you through the open window, “You look good in uniform!”

“What do you want, Winchester?” you replied with mock cordiality.

He frowned, “Oh c’mon, you aren’t still mad at me are you? It’s been years!”

You frowned back at him, harder.

“Hey, I’m Josh,” your friend said reaching across you to shake Dean’s hand, “I’ve heard so much about the legendary Winchesters! It’s nice to finally put a face with the name!”

“Can it, Josh,” you said. The way he was sucking up was making your stomach turn.

Sam finally chimed in, “Hey, (Y/N)! Sorry we didn’t mean to step on your toes here. Do you guys have a beat on what’s going on?”

“Werewolves. A pack. We got it!” You didn’t know why you were being short with Sam, it wasn’t his fault his brother was an ass!

“I love a good werewolf hunt!” Dean said with a gleeful smile.

You were about to repeat that you got it, but Josh interrupted, “Man there’s a lot of them. We got a few more hunters back at the hotel, but we sure could use some hunters like you to help.”

“Count us in,” Dean said as Sam nodded, “We’ll follow you back and talk strategy.”

Biting your tongue from saying anything you might regret, you stared straight ahead, your knuckles white on the steering wheel.

“See you in a bit, sweetheart!” Dean exclaimed with a wink before heading back to his overcompensation of a car.

 

*****

 

Your group of friends were all a little green compared to the Winchesters. They had been doing this their whole lives, but most of the group you had assembled had only been in the life for a few years. You had more experience than the rest, but the Winchesters still had miles and miles on you. You tried to make it clear that you were running the show, but the rest of Josh’s buddies were just as star-struck by the brothers as he was. It was starting to really get on your nerves. Dean Winchester was up to his old tricks, and before you knew it, he was taking the control away from you again. Seething, you tried to wrangle it back, but the group was too enamored with the seasoned vet to pay you any mind. It was inevitable that you had to let go of the reigns and fall in line. You didn’t have to be happy about it though.

With seven of you the raid went off without a hitch, and the members of the werewolf pack were eliminated cleanly; only minimal injuries to attend to. Josh and his friend Earl invited everyone for celebratory drinks in their room, and to your dismay, the Winchesters decided to take him up on the offer. You were inclined to just go to your room and get the night over with, but Dean had already made you look weak once tonight, and you weren’t going to let him do it again.

The group crowded into the small hotel room and cracked open beer after beer as they exchanged hunting stories. You were three bottles in when Candice, Earl’s girlfriend brought out the Truth or Dare cards. Apparently, this was a game they liked to play to break the ice with new friends, but you were sure this was going to be disastrous.

“Yeah, thanks,” Dean announced, “but I think it’s time for us to go.”

Candice whined and tried to explain how much fun it would be, but Sam and Dean clearly looked uncomfortable about the idea.

“What’s the matter, Winchester? Are you afraid of a little game of truth or dare?” you mocked him.

That smug smile of his returned and he pulled up a chair and motioned for Candice to start the game. Sam reluctantly sat back down on the couch.

The first few rounds were pretty tame, most of the dares were pretty silly so they had a few laughs, but then the dares got a little saucy. It was your turn to pull a card, and of course you got “Dare”. You took a sip from your beer and read the card aloud. “Dare: Choose one of your opponents and suck on a part of their body.”

All the males in the room perked up as you eyed the crowd. It was then that you heard Dean Winchester mutter under his breath, “I wouldn’t say no to that.”

You focused your gaze on him steadily and an idea popped into your head. He had a habit of humiliating you, and tonight was no exception. Maybe it was time to give him a little pay back. With another swig of your beer, you set the bottle down on the table and walked over to where Dean was sitting, he looked up at you with that stupid smirk as you stood above him. The room grew silent as you got down on your knees in front of him, keeping your eyes on his intently. You could have sworn you saw him gulp as you ran your hands up his thighs, spreading them slightly so you could wedge yourself between them. When you drew your hands back, you hooked them behind his knees and yanked, sliding him down further in the chair.

“Hey, I’m down for this,sweetheart, but don’t you think we should get our own room or something,” he said with his signature, macho bravado.

“Yeah, (Y/N),” Josh piped up, “We don’t need the free porn.”

The comment earned a slap from Earl and the other hunter, the quiet one, Randy. Apparently they were going to enjoy the show.

You kept your gaze on Dean’s pretty green eyes and said, “Don’t worry, you won't see much, and I’m sure it’ll be quick.”

The room erupted in jeers and Dean Winchester’s face flushed red with anger, and just a hint of embarrassment. You had him right where you wanted him.

You leaned into him and slid your hands back up the denim covering his thighs and smoothly reached down, grabbing his hand and bringing his fingers to your lips. You straightened up as you curled three of his fingers down, leaving his index and middle finger erect and placed the fingertips at your lips. Parting your lips slightly, you pulled his fingers into your mouth and bobbed your head back and forth as you sucked on his digits. The room had gone silent again as you worked his fingers in your mouth, and when you finished, you stood up with a satisfied smile to the sound of a long, low whistle from Randy.

“Damn, girl that was hot!” he said breaking the tension before motioning towards Dean, “Man you might want to put a pillow over your lap to cover that up!”

The room erupted in laughter as Dean realized he now had a very noticeable bulge in his pants. Candice gave you a high-five and you could see the rage behind Dean’s eyes. For a second you felt a little bad about it, but then you remembered how he always made you feel stupid and inadequate, and any pity for him vanished.

It wasn’t long before the game wound down, and you had to give Dean credit for sticking around after that. Finally, everyone departed and went back to their own rooms for the night. You had just gotten out of the shower and put your pajamas on, when you heard a knock on your door. The peephole was too high up for your short frame, so you opened the door to reveal your late-night visitor. It was Dean Winchester. “Oh, it’s you,” you said as you casually walked away, leaving the door open for him to come in, “What do you want?”

He slammed the door, startling you, and you spun around to face him.

“What the hell was that earlier?” he asked, a tinge of anger still resonating in his voice.

“Oh, I’m sorry, did I hurt your feelings?” you asked, your voice dripping with sarcasm.

He scoffed, “You’re a little brat, you know that? I ought to take you over my knee and spank you like the child that you are.”

Not backing down from a challenge, you walked straight up to him, and looked up defiantly into his eyes. “I would love to see you try, Winchester!”

“Don’t tempt me,” he said through clenched teeth.

You smiled up at him, “I dare you!”

Before you could even blink, Dean Winchester had you up and over his shoulder as he carried you toward the red and black diamond bedspread. You fought him the whole way, managing to clip him in the jewels with your foot. He stopped and grunted for a second, but his grip on you only got tighter. “You’re gonna pay for that,” he said as he flipped you onto the bed and turned you onto your stomach. His strong hands gathered your arms behind your back and you could hear the clinking as he unhooked his belt buckle.

“What are you doing?” you asked, mildly alarmed. Then you felt the leather from his belt wrap around your wrists, and tighten until you couldn’t move them anymore.

“Hey, you dared me!” he exclaimed.

“I dared you to try and spank me, not truss me up like a chicken dinner”

“How else am I gonna get you to cooperate?” He retorted, as he picked you up and laid you over his lap face down. 

In one quick motion he yanked your cotton shorts and your panties down exposing your bare ass. The next thing you felt was the sharp, stinging snap of his rough hand on your right cheek.

“Are you going to say you’re sorry, little girl?” he asked.

You were not giving him the satisfaction of an apology, so you kept your mouth shut.

Two quick slaps landed hard on your rear making you squirm a bit at the pain. You grit your teeth to avoid showing him your distress.

He scoffed, “You are so stubborn! Just apologize and I’ll stop!”

You took a deep breath and lifted your head up in defiance. A light chuckle fell from his lips to your ears before his hand came down again, harder. It made you flinch this time, but you wouldn’t budge. The next one was harder still, and you closed your eyes, trying to shut out the soreness that was beginning to form. The slaps came faster and harder until your ass became numb from the repetitive blows. At that point all you could hear was the slapping sound of skin on skin and you became aware of the hard lump below you in Dean’s lap. You were beginning to become oddly aroused yourself, but you couldn’t bring yourself to acknowledge it.

“Have you had enough yet?” Dean asked.

“Doesn’t bother me,” you lied.

“Okay,” he said, “you asked for it.”

The brief break had brought the feeling back to your skin, and his hand fell on you four more times. The fifth blow elicited a pained yelp and the spankings stopped. His hand laid tenderly on the red, raw handprint he had left behind. You felt him massage your ass, and then his fingers traced light, soothing circles over your skin.

“You’re not going to apologize are you?” he said, his voice filled with more tenderness than before, “You’d let me beat you to death before you’d give in, wouldn’t you?”

You tried to hold it back, but a tear trickled out of the corner of your eye involuntarily. It was the stinging of your backside, and maybe a little of your lost pride that caused it to fall.

Dean shushed you as he rubbed his hand over your cheek, “I’m actually kind of impressed you lasted that long! Let me make it up to you.”

Dean’s fingers trailed lightly down the curve of your ass and slid into the wet folds underneath you. You heard the sharp intake of his breath as he realized how wet you had become, and it wasn’t long before his digits dipped into your core. He pumped them slowly in an out, and you finally gave him what he was waiting for: a long, pleasurable moan.

Suddenly, the room became upright, as he lifted you back up onto your feet. He began to unhook the belt from around your wrists, but you told him to leave it on. It was unexpectedly turning you on. You felt his lips caressing your neck and you tilted your head to give him better access. The hand that was just being harsh against your bare skin, was now trailing gingerly down your arm.

“I don’t want to make nice, Winchester! Just fuck me already!” you demanded.

His hand gripped your arm tightly and he pulled you back into him forcefully before whispering in your ear, “Who knew a little thing like you would like it so rough?”

Chills went down your spine in anticipation, and you didn’t have to wait long before you were pushed over onto the bed. Dean’s strong hands molding you into the position he wanted you in; face down on the mattress with that now rosy ass up in the air. The sound of his zipper coming down made you moan again, and you could picture the smile that spread across his face. Without warning he thrust his cock into you from behind and bottomed out inside you. His grunt mimicked your groan, and he slowly began to pump in and out of you, getting a feel for your contours.

“Fuck (Y/N), you are so tight!” he exclaimed appreciatively as you pushed back into him further.

He took the hint and grabbed ahold of your hips, steadying you as he pounded into you faster and faster. Sweat began to bead up on his skin, and his breathing became more and more labored.

“Harder, Winchester!” you wailed, “Punish me!”

“You are such a bad little girl,” he replied, playing his role in your game. His fingers wrapped into your hair and he yanked, hard, pulling your head back off the bed as he continued to plow into you. “Do you like that, sweetheart? You like it rough?”

You moaned throatily in response and it only egged him on. His tempo slowed as he pushed into you forcibly, trying to get as deep into you as he could. Then he suddenly pulled out, leaving you feel empty and on edge.

“What the hell, Winchester!” you complained.

He laughed at your sudden eagerness for him. “Be patient, sweetheart, I’m not done with you!” You felt the restraint at your wrist disengage and your shirt was pulled up over your head and tossed aside. Dean turned you onto your back and attached his mouth to your breast, sucking and pulling at the nipple sharply. You sucked air in through your teeth at the sensation and you felt his lips turn up into a smile against your flesh. His mouth made its way down to your dripping pussy and he ran his tongue up and down your folds tasting your juices and making you moan in delight. You felt his tongue flick roughly over your clit, sending a shockwave through your body, and he lingered there, lightly circling your bud with his tongue and driving you crazy in the process. You whimpered slightly, the need becoming stronger and stronger.

“What’s the matter (Y/N)? Do you want to cum?” he teased.

“Dean please!” you squealed. It was the first time you called him by his first name, and it drove him over the edge.

He lifted your legs up over his shoulders and planted his face firmly into your womanhood, sucking at your clit with abandon until you felt that familiar explosion in your belly and the world around you began to spin, making you light-headed as you came down from your orgasm. The sounds you were making made Dean jealous, and he was going to claim what he needed from you now.

He pushed himself up on the mattress and lined his cock up at your opening again, slowly entering you to readjust to the grip you had on him. Your legs were still hooked over his shoulders, and he leaned into you to open you up further to him. When he was satisfied with the angle, he began to thrust into you harder than before, furiously working against the friction of your walls. As he got near his orgasm, he wrapped one hand around your neck and squeezed, just enough to cause your breathing to become shallow. It created the most amazing feeling of euphoria inside you and you felt that rubber band in your gut twist again, pulling and stretching until it couldn’t stretch anymore. You screamed his name in ecstasy and with a final thrust to send him over the edge; Dean quickly pulled out and spilled his seed all over your stomach, stroking his cock in his hand to help it along.

You felt the bed dip down as his body fell next to you in exhaustion. The two of you laid there for a moment as you recovered, and then he got up and walked into the bathroom, giving you a nice view of his naked, muscular ass as he walked away from you. When he returned he cleaned the cum off your belly with a washcloth, and then pulled the sheets down, maneuvering you under them and then taking his place next to you. He snaked his arm under the back of your neck, but didn’t pull you close. It felt like hours that you laid there next to each other staring at the ceiling without talking. You were replaying the experience over and over in your mind, and you realized that you weren’t mad at him anymore. That fire was replaced by the heat that was now building in your core again. With a smile you rolled over on top of him, straddling his hips. He smirked up at you with that annoying arrogance again.

“Truth or dare, Winchester?”


End file.
